Up until January 2015, I was either a child, a student, an employee or a traveler.
Zeroing in on the times when I was earning a paycheck, I always relied on someone else setting the rules of engagement, defining how work was to be done and gratefully accepted the paycheck (and bonuses, and stock grants) I would be handed every now and then.
My list of jobs has included: lifeguard at my high school, hawking my class notes to other students for $20 a class (legally!), working in the accounting department of a global airline (in midtown Manhattan), setting up offshore funds for uber-wealthy people at Merrill Lynch and finally, for almost 14 years: strategizing, creating and dreaming up the future in a variety of product planning, product management and marketing roles at Microsoft.
In all of the above cases, someone else handed me a paycheck. Then, I left it all behind and backpacked the world with my wife for over a year, during which time I had zero income.
Since 2015, things have been different. I’ve been doing my own thing. I thought I would fit right into the masses of entrepreneurs out there. What I’ve discovered is very different.